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HomeWikipedia List > Wikipedia

Wikipedia

Pauson-Khand reaction

The Pauson-Khand reaction is a chemical reaction in which alkyne, alkene and carbon monoxide are bound in a [2+2+1] cycloaddition to form a α,β cyclopentenone.

The catalyst used when it was first reported was dicobalt octacarbonyl (Co2(CO)8), but other catalysts have come to be used from later research.

Regioselectivity is a problem in intermolecular reactions with asymmetrical alkenes and alkynes as substrates, like in the example above.

Regioselective cyclization occurs in intramolecular reactions, such as in the example below.

Wilkinson's catalyst (RhCl(PPh3)3), which is based on the metal rhodium, uses trifluoromethanesulfonic acid (AgOTf) as a co-catalyst to advance a Pauson-Khand reaction.

Molybdenum hexacarbonyl (Mo(CO)6) works as a carbon monoxide source.

It is added to allene and alkyne, then heated and cyclized in dimethyl sulfoxide.

When iron is decomposed using ceric ammonium nitrate (CAN) in a cyclobutadiene iron (0) complex, [2+2+1] cyclization spontaneously advances, and a condensed-ring compound is produced.

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Date of last update:2013-10-25 16:46:13 jewel 1thumbs up   del.icio.usに追加   はてなブックマークに追加   twitterに投稿   facebookでshare
[ Original text ] https://ja.wikipedia.org/w/index.php?title=%E3%83%9D%E3%83%BC%E3%82%BD%E3%83%B3%E3%83%BB%E3%82%AB%E3%83%B3%E3%83%89%E5%8F%8D%E5%BF%9C&oldid=34406629 Permission is granted to copy, distribute and/or modify this document under the terms of the GNU Free Documentation License,
Version 1.1 or any later version published by the Free Software Foundation;
with the Invariant Sections being LIST THEIR TITLES, with the Front-Cover Texts being LIST, and with the Back-Cover Texts being LIST.
A copy of the license is included in the section entitled "GNU Free Documentation License".
GNU Free Documentation License
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